Have you ever been in an awkward situation where you just didn’t know what to say?

Maybe you were at a networking event or cocktail party trying desperately to make conversation with a room full of strangers.

Or stuck on a 30-floor elevator ride with the CEO of your company.

Or just sitting next to a distant cousin at Thanksgiving about whom you know nothing.

You try to start a conversation with the traditional, “How are you?” — which only gets you the even more traditional, “Fine.”

How can you get the other person to open up and engage in a more successful conversation?

One simple tip for better conversations

For me, one of the biggest tips is asking more open questions. They make conversations flow naturally. If you follow this simple rule, your conversations (at work and at home) will improve.

If you struggle to engage in successful conversations you will often find that you are asking too many closed questions. A closed question is one that requires only a yes or no answer, or a very short answer, in response. For example, “Did you go on vacation this year?” and “Where did you go?” are closed questions. Both can be answered with a simple one-word answer, in this case the answers could be “Yes” and “Florida”.

Instead, an open-ended question naturally lends itself to a longer answer and further conversations — which is what you want when you’re trying to strike up a conversation with someone.

Asking the right questions

Even if you’re just talking to your neighbor or coworker the technique of asking a simple, thoughtful, open-ended question can drastically improve your conversation skills.

For example, “Do you like books?” is a closed question. However, “What’s the best book you’ve read recently?” is more engaging and lends itself well to open-ended follow-up questions, so if the person merely names a book, you can ask, “What did you like about it?”

Here are some very simple ways to help you ask more open-ended questions:

  1. Start a question with “What do you think about…” this signals very clearly that you want more than a simple one-word answer.
  2. Another good starting phrase is “Tell me about…”. These words also send a signal that you are passing the ball over to the other person and expect them so say a little more than the bare minimum. Great ones that work for me are: “Tell me how you chose this career?” or “Tell me about your home city”.
  3. “How does this make you feel” is also very powerful. It’s a question that goes a little deeper and touches the emotions and feelings of the person you are speaking to. For example: “How do you feel about the restructure?” or “How does this [recent event] make you feel?”
  4. “What do you enjoy most / or least about…” is another easy way to ask open questions. For example, “What do you enjoy most about your job?” or “What do you enjoy the least about working here?”
  5. Another great trick is to follow up a short answer with a “Why?”. For example, if the question was “What do you think about the candidates in this election?” and you get back “Not much”, then you can simply follow up with “Why?” or “Tell me more”

Prepare for successful conversations

So many people get scared at networking events, at work – especially with the boss or even in social situations. Preparing some open questions will give you a heads up the next time you’re in one of these formerly awkward situations.

Some good open-ended questions might include:

  • How did you meet (the host of the event)?
  • What’s your favorite way to spend the weekend?
  • Why did you move to this city?
  • How did you get to where you are today?
  • If you had the perfect job, what would it be?
  • How does someone get into that job?
  • What do you enjoy most / least about living in New York?
  • What do you want to be doing in 5 years time?

Ask questions about things that matter

It’s also great to ask people about things they care about: their kids, their pets, their hobbies and collections. Compliment something about them, their clothes, their home or office and ask a question, like “I love those shoes. Where did you get them?” Stay away from controversial or political topics if you want to keep the tone light.

And Don’t Forget to listen

Finally, don’t forget to actually listen to the answers. Many times in conversation, we’re so busy thinking about how we’re going to respond, what we’re going to say next, that we forget to actually listen to the person in front of us. Truly giving another person your undivided attention is a rare gift, and will make you stand out as a great conversationalist.

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